Syntheses of medium-sized cyclic ethers from carbohydrates via an intramolecular nitrile oxide-alkene cycloaddition strategy

Tony K.M. Shing, Yong Li Zhong

研究成果: Article査読

16 被引用数 (Scopus)

抄録

Theregioselectivity of intramolecular 1,3-dipolar cycloadditions of nitrile oxides prepared from 3-O-alkenyl-1,2-O-isopropylidene-α-D- pentodialdofuranoses is dependent on the length of the alkenyl chain. 3-O-Homoallyl nitrile oxide afforded exo-cyclization oxepane exclusively. 3-O-Pentenyl nitrile oxide produced a mixture of exo- and endo-cyclization adducts (oxocane and oxonane) whereas 3-O-hexenyl, heptenyl, and octenyl oxides all gave endo-cyclization adducts (ten-, eleven-, and twelve-membered cyclic ethers, respectively) exclusively.

本文言語English
ページ(範囲)1205-1208
ページ数4
ジャーナルSynlett
8
DOI
出版ステータスPublished - 2006 5月 15
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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